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The ongoing Western support to Ukraine’s security sector reform requires the assessment of the reform success. This article considers whether Ukraine’s reform is achieving effectiveness, efficiency, and democratic governance objectives. The author uses a theoretical framework of complexity theory applied to the change management research in organizational studies. The application of this framework is appealing from the perspective of complex and chaotic organizational contexts, in which the security sector can stimulate the emergence of ‘strange attractors’ for system’s adaptability. The findings suggest that Ukraine is building a shared vision following up on chaotic-framed Security Sector Reform acceleration since 2014. The gap between increased confidence in the volunteers and the army and declining confidence in general government institutions, economic burden, and Western cohesion issues constitute the risks that Ukraine’s Europeanization faces.